Despite Singapore’s huge effort to promote entrepreneurship, entrepreneurial spirit is still lacking. Entrepreneurial intent is especially low among Singaporean young adults who prefer a traditional career path. A psychological barrier, fear of failure (FoF), has been proposed as an explanation. In the entrepreneurship context, FoF is generally assumed to be a unidimensional construct. Although FoF has been examined in relation to the processes of established entrepreneurs, it has not been explored in relation to entrepreneurial intent, and no studies have examined its dimensionality in this context. We explored this possibility using a qualitative approach and the cognitive–motivation–relational theory of emotion. Inductive thematic analysis of 35 semi-structured interviews revealed three main concerns about business failure: financial, psychological, and career. The analysis challenged the prevailing view by supporting the multidimensionality of FoF in entrepreneurship, established its relevance as a barrier to entrepreneurial intent, and highlighted potential cross-cultural variation in FoF.